We pass a number of fanciful towns and hamlets. Recently we've come through Hayter's Gap, Haysi, Pippa Passes, and even upcoming Krypton, Kentucky looms. However Dwarf, Kentucky has be on anyone's short list (tee hee hee) of great names.

It's really just a tiny burg with a post office, fire department, and a few buildings. The community board is up but still advertises the Dwarf 2012 Reunion.

Hazard, Kentucky

Brief stop here in Hazard where coffee is $1.05 and the wifi options include “KILL WHITEY” and the “Satanic Temple of Hazard.”

Bree our waitress made a nice smiley face of pineapple and strawberries with my cottage cheese. Here we have the accent, but Bree's Kentucky drawl is infectious but difficult to understand. Our table asked several times what kind of pie, and she kept repeating the answer until I told them it wasn't Kentucky Seal but Kentucky Silk. I asked her for water in my bottle and she kindly asked if I wanted “ahss” in it.

Meeting Mayor Charles Long

At 97 years old, Booneville Mayor Charles Long is the oldest serving Mayor in the United States. He may also be the longest serving Mayor as well, having first been elected in 1959 back when Dwight D. Eisenhower was President and Fidel Castro had just taken power in Cuba.

He has never had a contested race for re-election.

“That tells me one of two things Mayor,” I said, “Either you're really good at what you do, or the job is so horrible no one else wants it.”

“When I was elected we didn't have sidewalks. No pavement on the streets - just dirt. If you wanted to go to Jackson you had to ford the river. When I got on the town board in 1954 the city had a wheelbarrow, some shovels and axes for road maintenance. Now I have city water and sewage into 96% of the county.

The city - if you can call it that - has 81 residents according to the 2010 Census has seen a lot of changes. "I've never lived anywhere else (other than a stint in the Philippines with the Navy during World War II) and I just loved the people.” He was married to his wife 72 years. She passed way in 2012.

The next election is next year. “Will you run again,” I asked. “If I'm alive I will. I'll be 99.”

•••

Tonight we are staying at Booneville Methodist Church Life Center. It's a lovely night and the sunset lots up the sky all around us in a gauzy pink, blue and orange.

One other noticeable difference in Kentucky. The convenience stores have a bewildering supply of tobacco including massive bags of pipe tobacco.

I think what surprises most people is that it takes two weeks to go through Virginia. It is the longest State we pass through. Kentucky is eight or nine days. Illinois is a scant four or five and the includes a rest day.

So passing this state line is yet another little milestone of achievement earned.

Having left early I was on the the lookout for some of the later departing, but much faster, cyclists but thus far now one had overtaken me. After Ashcamp it started raining so I put on my jacket and started the first of five steep climbs. It was during that that that I felt and heard the sad (clunk) of a rear wheel spoke going out. I twisted it into place, loosed the back brakes and kept riding. The tire was holding out ok, but I was making slow progress. Reaching the top of the hill and coming down, I realized that I could not fully stop using the rear break and barely come to a stop using the front brake.

In Hellier, Phil, driving the van came by and I signaled him that I didn't feel safe coming down the hills until the spoke was fixed. So in the van I sit. 20 miles today.

Our first night in a state OTHER than Virginia. The differences between Virginia and Kentucky are immediate and unalloyed. There is a poverty here that is both proud and depressing.

Two things. We could not go ten miles without seeing some house, trailer, or dwelling utterly ransacked or burned and destroyed. At the Map Meeting the whole discussion is about how to handle both feral and let-loose dogs which make a sport of barking, chasing, or attacking cyclists. It's a problem that's worse here but may extend into Missouri.

After dinner tonight we met with Doug Naselroad, Master Luthier, at the Appalachian Artisans Center here in Hindman. He teaches people how to make a variety of acoustic instruments including the Appalachian Dulcimer. It's a beautiful instrument. The Artisans Center works to preserve Appalachian Arts, Music, and Culture.

A sense of place is terribly important here, Mr Naselroad tells of a student of his making a guitar from the wood scavenged from shelves of a family grocery that had served the valley. When he was done he had a beautiful guitar, but more important it had a story. “All stringed instruments should be made with wood that is a 100 years old and has a story,” Naselroad said.

Last ten miles dominated by three steep hills in the oppressive heat. Ugh. Fell asleep for a nap after my shower.

Listening to Bluegrass at the park amphitheater tonight courtesy of the Backwoods Boys where the introductions include which county you come from because it matters.

Large Amish family behind us. Norm introduced himself and we got to talking. They are originally from Northern Indiana and then Ohio but now from Eastern Kentucky. They didn't come here by horse and buggy, hiring someone to bring them here. We got to discussing the relative discomforts of traveling by bike versus by buggy. It's possible, the man said, to travel to New York Amish by buggy and keep to a route that gets you to an Amish Community every thirty or forty miles to take care of your horses but, he paused with a chuckle, not sure if you would like traveling that long by buggy.

The Breaks is known as the Grand Canyon of the South and the picture doesn't do it justice but there is a Canyon down there obscured by all the foliage.

Map Meeting. After every dinner we go over the next days maps and route. Tomorrow is 69 miles - really 70 plus and Philip says the Notes say it is the most challenging day with five large steep Kentucky hills. Plus I cook so I need to try to be at camp at 4pm.

Cycling with Norm from Damascus. He is such a good companion to have because he could easily just out bike me.

Despite all the problems I feel really good about this ride. My behind didn't really hurt - a testament to all of the lubes, and creams and glides - I am sure. After all of my showers I have been amazed that I am not screaming in agony any time I set down on that seat.

This is gorgeous country filled with ups and downs, the hollows and hilltops of Appalachian hill country. Most of the time we see cows, redolently grazing on green fields and hills. One farm was filled with donkeys and goats, and we see at the entrance it is called Little Ass Acres.

Water seeming everywhere. Every dip or hollow almost always results in a creek or river including this fabulous (but no longer running ) watermill.

After Hayter's Gap (pronounced Highter not HATER) the road turns up and stays going up but there was this great mailbox set up and as I was taking a picture a bird flew out of the left mailbox.

When I turned on Highway 80, the road crew had blocked it as closed, but they let the cyclists go through. When you get to the truck, you'll need to walk around it, he told me.

I thought it was road repair, but it wasn't. A truck carrying asphalt had taken a turn too sharply, and the rear wheels slid down, turning the asphalt container on it's side. Major clean up.

I had to portage not just around the entire truck but the multi-effort recovery and cleanup operation. Took this selfie in front of the state trooper car. Sent that to Gina who quipped that I must have gotten it for going too slow.

Slept deliciously in my hammock until I could hear the other Hostel residents begin to emerge including my co-hammock resident Aaron (Trail Name Mountain Man) and his improbably brave but appropriately named 14 ounce dog Critter begin to stir. Critter has a huge bell attached to his neck so it's like having a spastic mutant reindeer elf darting about the yard.

The Woodchuck Hostel, named after the lumbering bear of a man who has, thus far, only worn camouflage t-shirt, has almost every room crammed with beds. In the backyard there is a wooden crossed stands where four hammocks can be hung. There, blissfully I hung the entire night in the fresh air.

Beyond that, the Hostel experience is bewildering with a parade of hikers and bikers and Lord knows who else comes through the kitchen and common areas. Some have incredible poor body odor. The kitchen is a mix of public and private and the backyard porch is the laundry where the washer and dryer run constantly. The Woodchuck does not tolerate drugs or alcohol so I don't have to contend with marijuana smoke.

Rest Day, particularly the first rest day means shopping and tweaking. I bought a different pack at a wonderful 50% discount. Sun screen. I took my bike in for a safety check. All good. We are told that the day riding West means a large sustained pedal uphill.

Lunch today at Mojos for a vinegar based pulled pork sandwich. Very good. Met up with inspirational and young bikers and hikers Abigail and Seth who have been biking since Georgia. They also did the Appalachian Trail and while doing it and the current bike ride they collect and carry out the trash they find. Vibrant couple. Different paths. We took a group picture while I controlled the phone camera with my watch and was promptly given the Trail Name "Savvy."

Damascus, the Town, is a small Appalachian Village, of maybe a thousand people. However it is a major stop on both the Appalachian Trail and the TransAmerica Bike Route. It also has a vibrant bike and hiking trailer called the Virginia Creeper. This weekend the town hosts a Trail Days Festival and a tent city is beginning to swell the population to eight thousand.

Dinner tonight with the group at the lovely Old Mill Inn on their back patio overlooking mallards and a pond and a small waterfall.

Tonight's stop at the Woodchuck Hostel in Damascus, Virginia. It's an intersection of both the Appalachian Trail and the 76 TransAmerica Bike Route. Today 57.8 miles for a total of 476.8 Miles. 3635 feet up. 4042 down. The climb up was a relentless constant for two ten mile stretches but the last 15 miles were a mostly exhilarating coast down following the waters and waterfalls of the river into Damascus.

Our guides have stopped writing the day's agenda on the white board on the truck for a while now. So I decided to start putting up faux-agendas.

Sadly my bike's rear wheel needed to be swapped out so no biking for me today. Tomorrow is our second rest day.

The Millennium Falcons' FTL drive is down, Han's dead, so it's just Chewbacca getting it repaired with the great help of Eric of Mike's Hike and Bike. Hopefully rear broken spokes are a thing of the past.

Sadly my bike's rear wheel needed to be swapped out so no biking for me today. Tomorrow is our second rest day. Two of our group's loved ones came to join us for the extended rest stop. Jim's wife Judy whipped Cesar Salad and fried Salmon and Halibut. Judy also made creme brûlée.

Never ate so well in a skeevy motel parking lot.

Sharing a room with Mike tonight and tomorrow who announced with a satisfied sigh that he was really going to stink up the room. At first I didn't know how to respond other than, "How so?"

Lovely countryside filled with horses, cows, farms, and hills, hills, hills. If the hills are alive for me right now it's with shifting gears. When we do our rest day in Damascus, Virginia I will need to get them looked at because the transitions aren't as smooth as I like.

This is a country with broad economic scales. We get a stereotypical Appalachian Homes, ramshackle forms, and then Equestrian Centers, gorgeous houses with views of the valley.

POSTED - NO TRESPASSING are almost everywhere.

Stumbled upon this ruin of a silo, with a tree growing from the top, reminding my of the medieval tower in Lucca, Italy.

So many things to love about this little "welcome mat" before a long winding road up to a farm. The banners of two dogs, the flag, the iron wheel....where does one start and how do we know when to quit?

Parched. Really parched. We thought there would be a place for water in a town called Catawba but there wasn't. Of course for some reason I couldn't get the name Catawba to stick in my mind so I kept calling it, Caddywampus, Cowpie, Caddyshack, and Catadabadoo.

We reached it and there was no water and so we ride on and I'm getting parched. Saw this barn, with two quilt designs on it. Just lovely. Apparently Barn Quilts are a thing, and there are Trails set up to see them and the lovely countryside.

Except to me, right now, it's water, and hills. Eventually we went by a house where I saw a man get out of his truck, and I pulled up and asked if hem minded to let us use his hose to fill up our water bottles. Barry had just pulled up. He went into his house and came out with four cold plastic bottles of water.

We talked about the road ahead. It's mostly down, he tells us, until you get through a tunnel railroad overpass, and there's a Convenience store but then it's all up hill. "Until you get to the Ford Dealership.

Barry and I cycled on and got to the gas station / convenience store. By this time they have become an oasis. Lou was there, along with Bob from Minnesota. Bob, a wirey gray haired man is going east to west but on his own and hauling all his gear. He routinely passes us on hills.

We get a few milestones to look forward to during this trip. Miles traveled 407 so far. Weeks 1. States. Just 1. Maps Completed today 1.

We also had an unwelcome milestone. We lose Don tomorrow. At 74 he was one of my heroes. Unfortunately he had a prior biopsy site get infected and has been told no more bike riding.

It is a heartbreaking development for him because this was a dream for him. Don just enthusiastically embraced this trip. I recall him frantically waiting for some to get a picture of him at the entrance to the Blue Ridge Parkway. We have hopes that his condition will improve and he can return in a recumbent bike but he says that his wife has her thoughts and I know what that means. Wives tolerate this sort of adventuring machismo only so far and there is a Doctor at that line.

Lexington is famous for the Virginia Military Institute and the house of a former VMI instructor, Thomas Jonathon "Stonewall" Jackson. Here in the South Confederate heroes are loved and cherished, particularly like Stonewall because he was so good, so eccentric, and his death, like all death in war, tragic, but made all the more so because he was shot by one of his own sentries. He held on until the Sabbath, deeming it be a proper day for death. Pneumonia set in and he said, “Let us cross over the river and rest under the shade of the trees.” Then he passed away.

I doubt there is or was a Southern girl or boy who hasn't wondered what would have happened had Stonewall been there to help Robert E. Lee throughout the war. In many senses Stonewall represents the tragically self-inflicted (and once inflicted - inevitable) outcome of the Civil War.

When it's sunny out I'll go through eight 21 ounce bottles of water easily. I have two on my bike so I get them refilled anytime I can - usually by buying something and then asking, or just buying the water.

Convenience stores are like little Inns to us, filled as they are with water, Gatorade, and sometimes a local cafe inside.

Water Stop. 25 miles or so to go.

This was just down the road from Natural Bridges and this lovely piece of roadside kitch. I love the car "fer" sale - front end bent and crumpled.